Diisopropylethylamine → HCID 178513889、化合物

HRID 2420752ノート

反応式

HRID 2420752 の反応式
C(N(C(C)C)CC)(C)C.Cl.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24].I.[NH2:27][C:28]1[C:29]([C:36]([NH:38][C:39](=[NH:42])SC)=[O:37])=[N:30][C:31]([Cl:35])=[C:32]([NH2:34])[N:33]=1>C(O)C>[NH2:27][C:28]1[C:29]([C:36]([N:38]=[C:39]([NH2:42])[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24])=[O:37])=[N:30][C:31]([Cl:35])=[C:32]([NH2:34])[N:33]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 8663423712-Aminododecanoic acid amide hydrochlorideHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

生成物 1

HCID 178513889HCID 178513889、化合物収率 56.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Diisopropylethylamine (0.24 mL, 1.38 mmol) was added to a suspension of 12-amino-dodecanoic acid amide hydrochloride (8) (0.068 g, 0.27 mmol) in absolute ethanol (5 mL). The resulting solution was stirred at 70° C. (oil bath) for 5 min, after which time 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (115 mg, 0.30 mmol) was added in one portion. The reaction mixture was then stirred at this temperature for 3 hours then cooled to room temperature. After removal of the solvent by rotary evaporation the resulting residue was dissolved in small volume of methanol, and the solution passed through an ion exchange resin column (Dowex 550A OH type). The resin was rinsed with methanol and the methanol solution concentrated in vacuo to a yellow residue. This residue was stirred in a minimal volume of methanol and the resulting solid was collected by suction filtration and washed with a small amount of methanol to give 12-[N′-(3,5-diamino-6-chloropyrazine-2-carbonyl)guanidino]-dodecanoic acid amide 9 (0.065 g, 56%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) 1.23 (m, 14H), 1.49 (m, 4H), 2.01 (t, 2H), 3.11 (m, 2H), 6.65 (m, 4H), 7.21 (br, 1H), 9.06 (br, 1H). m/z (ESI) 427 [C18H31ClN8O2+H]+. mp 192-194° C.

後処理

  1. stirringThe reaction mixture was then stirred at this temperature for 3 hours
  2. temperaturethen cooled to room temperature
  3. customAfter removal of the solvent
  4. customby rotary evaporation the resulting residue
  5. dissolutionwas dissolved in small volume of methanol
  6. washThe resin was rinsed with methanol
  7. concentrationthe methanol solution concentrated in vacuo to a yellow residue
  8. stirringThis residue was stirred in a minimal volume of methanol
  9. filtrationthe resulting solid was collected by suction filtration
  10. washwashed with a small amount of methanol

出典と根拠

ORDレコード
ord-ad8776510ca24aebb56d112b08712315
出典データセット
uspto-grants-2011_06
特許番号
US07956059B2

反応ノート

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